Ethyl Acetate → 4-(3-Chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)-amino]-(3-methyl-3h-imidazol-4-yl)-methyl]-1h-quinolin-2-one

HRID 50185

Reaction equation

HRID 50185 reaction equation
[NH2:1][C:2]([C:27]1[CH:28]=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=1)([C:21]1[N:22]([CH3:26])[CH:23]=[N:24][CH:25]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.[CH:34](=O)[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1.[OH-].N.C(OCC)(=O)C>C(O)(=O)C>[Cl:20][C:16]1[CH:15]=[C:14]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:2]([C:27]4[CH:28]=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=4)([N:1]=[CH:34][C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=4)[C:21]4[N:22]([CH3:26])[CH:23]=[N:24][CH:25]=4)[CH:4]=3)[NH:9][C:8](=[O:13])[CH:7]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 120507296-[Amino-(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1H-quinolin-2-oneHCID 21862953Ammonia hydroxide

Product 1

HCID 120507304-(3-Chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)-amino]-(3-methyl-3h-imidazol-4-yl)-methyl]-1h-quinolin-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the title compound of example 42 (11.89 g, 25.03 mmol) in acetic acid (75 ml) was added p-anisaldehyde (6.09 ml, 50.06 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 4 hours after which time it was cooled to 0° C. 10 ml of ammonia hydroxide was added followed by addition of ethyl acetate. After separation, the organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to yield the crude product. It was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1 to 5:95:0.1) as eluents to afford the title compound of Example 43A as a white solid (11.58 g, 78% yield).

Workup

  1. temperaturewas cooled to 0° C
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customto yield the crude product
  7. customIt was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1 to 5:95:0.1) as eluents

Sources & evidence

ORD record
ord-60d4301b0661475eba687659c5701d38
Source dataset
uspto-grants-2004_03
Patent number
US06710209B2

Linked notes

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